Key West Walking Tours

45 Results
Southernmost Food & Cultural Walking Tour by Key West Food Tours

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in …More

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in...

3 hours Free Cancellation
4.9 (1,977)
from
$94
Key West Historic Seaport Food & Walking Tour

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood …More

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood...

3 hours Free Cancellation
4.9 (682)
from
$94
Key West Craft Cocktail Crawl

Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the …More

Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the...

3 hours Free Cancellation
4.9 (620)
from
$99
Jimmy Buffett Tour

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at …More

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at...

1 hour 30 minutes Free Cancellation
4.8 (321)
from
$79
Key West Historic Old Town Food Tour with 5 Authentic Tastings

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings …More

Likely to Sell Out
Likely to Sell Out

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings...

2 hours 30 minutes Free Cancellation
4.8 (312)
from
$108
Key West Historic Bahama Village & Hemingway Heritage

Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key …More

Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key...

1 hour 30 minutes Free Cancellation
5.0 (262)
from
$60
Southernmost Key West History and Culture Small-Group Walking Tour

Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience …More

Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience...

1 hour 45 minutes Free Cancellation
5.0 (135)
from
$54
Hemingway Food and Walking Tour

This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, …More

Likely to Sell Out
Likely to Sell Out

This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches,...

2 hours Free Cancellation
4.8 (109)
from
$99
The Hemingway Experience in Key West

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour …More

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour...

4 hours Free Cancellation
4.9 (73)
from
$189
Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, …More

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie,...

1 hour 30 minutes Free Cancellation
4.9 (62)
from
$70
PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during …More

Likely to Sell Out
Likely to Sell Out

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during...

90 to 180 minutes Free Cancellation
4.9 (22)
from
$55
Tropical Fruit Hunting Tour at Grimal Grove

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on …More

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on...

1 hour 30 minutes Free Cancellation
5.0 (21)
from
$41
2-Hour Live Music Guided Tour in Key West

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for …More

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for...

2 hours Free Cancellation
5.0 (20)
from
$35
iWitness Key West True Crime Walking Tour

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and …More

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and...

1 hour 30 minutes Free Cancellation
4.8 (19)
from
$49
Key West Historic Private Food Tour with 5 Authentic Tastings

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings …More

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings...

2 hours 30 minutes Free Cancellation
4.8 (19)
from
$145
Key West: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most …More

Likely to Sell Out
Likely to Sell Out

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most...

1 hour Free Cancellation
4.9 (7)
from
$45
Key West: Private Vacation Photoshoot with Photographer

⭐ Top-Rated Vacation Photoshoots 2025 & 2026 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of …More

⭐ Top-Rated Vacation Photoshoots 2025 & 2026 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of...

1 hour Free Cancellation
5.0 (6)
from
$78
History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local …More

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69
Key West Odyssey: Uncover Island Secrets, Walk by Locals

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic …More

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic...

1 hour 30 minutes Free Cancellation
5.0 (2)
from
$60
Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

Likely to Sell Out
Likely to Sell Out

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$49
Dark Corners of Key West Private Walking Tour

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s …More

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s...

2 hours Free Cancellation
5.0 (1)
from
$152

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